Westley (not Wesley) is the dream hero in The Princess Bride written by William Goldman, and he is played to absolute perfection by Cary Elwes in the movie version. In the movie, he dresses in a very suave, black, swashbuckling outfit that is the ideal clothing for a person who wants to look just like a confident and romantic hero.

This 'man in black' or Dread Pirate Roberts outfit is very appealing just on its own but would also look perfect matched up with a Princess Buttercup or Inigo Montoya costume to make a Halloween or cosplay duo.

Starting off as a simple farm boy, this guy has an amazing transformation into a fearsome pirate and becomes a hero that uses his wits, swordplay skills, and strength to overcome all obstacles to save his one true love, Buttercup. Read on to find out how to transform yourself into the Man in Black right here.

Step 1 - Start Here with Westley's Head and Eye Gear

Solid Black Bandana Head Wrap

This looks exactly like the bandana head wrap or skullcap worn by Westley in The Princess Bride movie which covers his blonde hair and is knotted at the back with the excess ties of the black cotton material hanging down. In fact this particular one actually has been worn many times by reviewers for exactly that purpose.

Westley wears a plain black bandana and eyemask, essential for his Dread Pirate Roberts look! Zorro eye and head gear is often the perfect match for the Man in Black! Sometimes you get the eye mask and head wrap in one costume piece which is nice and easy.

Dread Pirate Roberts Black Eye Mask

Cary Elwes who played the part of our masked hero, also wore a black eye mask to conceal his identity. The eye mask is just plain black like this one. He looks so much cooler with the eye-mask on. It adds a real air of mystery about him. I haven't manged to locate a really good quality eyepiece so this one just does the job. You might find something better if you have a good look.

Step 2 - Add an Appealing, Sexy Lace Up Shirt!

Black Shirt with Laces: Just the Thing to Get Hearts Racing!

His shirt has a laced-up front and puffed-out long sleeves. Here are some pirate style shirts both of which look similar to the long-sleeved one worn by Cary Elwes in the movie with its lace-up front and puffy, balloon sleeves that end in tight cuffs around the wrists. Look for a basic costume shirt in black with a lace up front and sleeves that balloon out in the arms but end in tight cuffs.

Black lace-up pirate shirt | Source

Step 3 - A Dread Pirate Sword and Sword Belt

Rapier Steel Swords - Or the Movie Prop Replica!

Lots of people dressing up as our hero decide to use an adult-sized rapier sword for their outfit - just be aware that these will have sharp points and they are not toys. Rapiers are often used as a costume prop by actors and those dressing for Cosplay events. They are far nicer and more elegant than a toy plastic sword. I have picked out a couple of decent options below for you to view.

The actual movie prop sword is now an expensive collectible and would be a hefty purchase for Halloween and even cosplay events. However, you might want to get a closer look at the replica from the movie so you can see exactly what you're looking for in a sword for our Princess Bride hero. I'd love to have this particular sword as well as Inigo's. They make an awesome memento for fans like me.

Rapier Sword Frog Belt Hanger

If you're buying a rapier sword for your costume, you'll need a frog belt hanger so you can keep the sword hanging off your belt to look like the Dread Pirate Roberts. Having this hanger fits with the style of the outfit and it means that you don't need to hold on to the sword all the time while in character.

A frog hanger is a belt for your sword | Source

Step 4 - Long Dread Pirate Boots and Black Pants

Black pirate boot tops coverings | Source

Pirate Boots for Our Hero

Westley's pirate boots are long, rather plain black leather boots which don't quite come up to his knees. Like lots of pirate boots, they have a rolled top although this doesn't flare out like some extravagant and flamboyant boots do.

They are fairly plain and are without any laces. These have a good styling but they don't have the best reviews so also check out the covers I mention below as a less expensive option.

Pirate boot top covers are ideal as an inexpensive dress up option and for getting the right look and style for your costume. Pop these over the top of some plain black shoes and transform yourself into character! These do exactly the right job and give you just the look you need.

Some Plain Black Pants / Trousers

You'd Look Silly Without Them! The sexy and suave 'Man in Black' outfit requires some plain black pants or trousers. You've probably already got some that you can use. Westley's pants are not skin tight like leggings but they are a slim fit and tuck down into his long boots.

Step 5 - The Rather Crucial Costume Accessories

3 Extra and Important Outfit Accessories

Westley keeps his hands covered over in plain, leather-like black gauntlet gloves that just cover over the bottom of his shirt cuffs so you don't actually see any arm skin on his outfit.

It is important that he dresses head to toe in black and that's why another moniker for him is The Man in Black! It gives him a really dramatic and also stylish appearance and takes his status as a feared and unknown pirate to an absolute extreme.

Westley wears a wide, black fabric sash belt tied around his waist. The ties hang down very low, one tie down to his knees and the other further up at thigh level. You can of course get some plain black cotton fabric and make a belt yourself. It's just an extremely long rectangle shape which you can knot around the waist. Over the top of the sash, Westley wears a medieval style ring belt which is a standard piece of clothing with a man's medieval costume.

Black Pirate Costume - A Workable Match

This Blackheart Pirate Outfit from Amazon could work OK. It includes a black, lace-up shirt, bandana, boot covers, black belt and wrist cuffs. You will still need a black eye mask, black gloves, pants and a costume sword to pull off the right look. If you're in a real hurry to order and not too worried about the exact look then this would be an okay option - but you'd be better following all the individual elements I show you on this page.

Most of what you need to pull off a Westley, Dread Pirate look! It is nowhere nearly as good as pulling all the individual elements together but will do if you are lazy or needing something in a rush. You will still need certain parts like the eye-mask to pull it off.

My Princess Bride Hero! If you've pulled off your outfit correctly, you should look just this sexy!

Here's The Princess Bride Man in Black | Source

I know a ton of females like myself who drool over the Man in Black from The Princess Bride. Never mind the simple but cute farm boy, he's OK but he's not really going to get many hearts racing. Nope, being dressed up as the fearsome hero and hiding behind that mysterious mask is as sexy as it gets.

That's why I had to create this costume page because I wanted men out there to see what the ultimate male costume is. This is it, guys! Note that women and kids can also learn how to dress just like Westley using the very same step-by-step process. I hope you've enjoyed reading this hub today, thanks for your visit. Hope you have lots of fun dressing as this cool character.

Dress up as Westley, the Dread Pirate Roberts hero for cosplay or Halloween | Source

Your Comments - Will You be Dressing up as Westley?

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Oneshotvariety LM

6 years ago

Very cool costumes! Unique for sure!

anonymous

6 years ago

One of my favorite movies of all time - love the Dread Pirate Roberts Costumes!

AUTHOR

Marie

6 years ago

@kburns421 lm: Thank you Kburns ;)

kburns421 lm

6 years ago

I am one of those drooling women you mention :-P This would be a great costume for men.

AUTHOR

Marie

6 years ago

@Wendy Leanne: Thank you so much, ThrivingMom :)

Wendy Leanne

6 years agofrom Texas

Love it! The Princess Bride is my favorite movie of all time. *~blessed~*

AUTHOR

Marie

6 years ago

@FlynnTheFineFle: Yes tall boots can be very expensive. Have a look for some black pirate boot tops for Westley's Dread Pirate Costume instead - these are far more affordable and give the impression of boots which you can just wear over normal shoes.

FlynnTheFineFle

6 years ago

So cool. It's a shame that the boots are more expensive than a sword. I already have the sword...

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